GB833666A - Aldehyde condensation reactions - Google Patents

Aldehyde condensation reactions

Info

Publication number
GB833666A
GB833666A GB19399/56A GB1939956A GB833666A GB 833666 A GB833666 A GB 833666A GB 19399/56 A GB19399/56 A GB 19399/56A GB 1939956 A GB1939956 A GB 1939956A GB 833666 A GB833666 A GB 833666A
Authority
GB
United Kingdom
Prior art keywords
reactor
water
catalyst
aldol
condensations
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB19399/56A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Celanese Corp
Original Assignee
Celanese Corp
Celanese Corp of America
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Celanese Corp, Celanese Corp of America filed Critical Celanese Corp
Publication of GB833666A publication Critical patent/GB833666A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/75—Reactions with formaldehyde

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Aldol-type condensation products are prepared by the method claimed in the parent Specification in the presence of a volatile tertiary amine as sole catalyst, the condensation being effected under a pressure above atmospheric and the reaction mixture containing more than 19% by weight of water. This procedure allows of the use of higher temperatures, e.g. 80-90 DEG C. Preferably, the reactants, amine catalyst and water are passed through a reactor in which the pressure is superatmospheric and then passed to the top of a distillation column; unchanged reactants, water and amine catalyst are removed overhead and returned to the reactor and the aldol-type products are removed as bottoms. The procedures and apparatus described in the parent Specification may be utilized, the reactor being provided with a valve on its outlet whereby the reactor may be operated at elevated pressure and the distillation effected at ordinary pressure. The aldol-type condensations, classes of reactants and amine catalysts are as described in the parent Specification and the products may be catalytically dehydrated by the methods and in the apparatus described therein. Examples describe the auto-condensations of acetaldehyde and butyraldehyde and the condensations of acetone and methyl ethyl ketone with formaldehyde, the reactions being operated continuously in the presence of 19.4% upwards of water and trimethylamine or triethylamine as catalyst, the reactor temperatures ranging from about 55 DEG to 86 DEG C. and the pressures from 20 to 60 p.s.i.g.; the aldoltype condensation products are subsequently dehydrated to yield corresponding unsaturated aldehydes or ketones by heating with aqueous phosphoric acid.
GB19399/56A 1955-06-23 1956-06-22 Aldehyde condensation reactions Expired GB833666A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US833666XA 1955-06-23 1955-06-23

Publications (1)

Publication Number Publication Date
GB833666A true GB833666A (en) 1960-04-27

Family

ID=22177845

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19399/56A Expired GB833666A (en) 1955-06-23 1956-06-22 Aldehyde condensation reactions

Country Status (1)

Country Link
GB (1) GB833666A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1957301A1 (en) * 1968-09-27 1971-05-19 Basf Ag Process for the preparation of beta-hydroxy aldehydes
DE1793512A1 (en) * 1968-09-27 1972-02-10 Basf Ag Process for the preparation of 2,2-dimethyl-3-hydroxypropanal
CN110759821A (en) * 2019-11-23 2020-02-07 张家港市华昌新材料科技有限公司 Neopentyl glycol production raw material recovery system and recovery method thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1957301A1 (en) * 1968-09-27 1971-05-19 Basf Ag Process for the preparation of beta-hydroxy aldehydes
DE1793512A1 (en) * 1968-09-27 1972-02-10 Basf Ag Process for the preparation of 2,2-dimethyl-3-hydroxypropanal
CN110759821A (en) * 2019-11-23 2020-02-07 张家港市华昌新材料科技有限公司 Neopentyl glycol production raw material recovery system and recovery method thereof

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